4425-23-4Relevant academic research and scientific papers
SYNTHETIC ANALOGS OF Peganum ALKALOIDS VI. PHOTOCHEMICAL OXIDATION OF 2,3-POLYMETHYLENEQUINAZOLINE DERIVATIVES
D'yakonov, A. L.,Telezhenetskaya, M. V.
, p. 460 - 463 (1991)
The rates of the photochemical oxidation of quinazoline alkaloids - deoxypeganine, peganine, pentamethylenequinazoline, and peganol - to the corresponding oxo derivatives have been studied.It has been shown by HPLC that the oxidation of deoxypeganine proceeds through a stage of the formation of a carbinolamine (peganol); in the case of its hydrochloride, the reaction takes place by the same scheme but four times more slowly.Tetra- and pentamethylenequinazolines have been synthesized and information on their melting points in the literature has been corrected.In the series trimethylenequinazoline-pentamethylenequinazoline -tetramethylenequinazoline the stability falls from left to right.
Peroxide-Mediated Oxidative Radical Cyclization to the Quinazolinone System: Efficient Syntheses of Deoxyvasicinone, Mackinazolinone and (±)-Leucomidine C
García-Ramírez, Jazmín,Miranda, Luis D.
, p. 1471 - 1477 (2020/11/30)
An efficient protocol for obtaining fused quinazolinones through an oxidative free-radical cyclization under metal- and tin-free conditions is described. The oxidative cyclization of various N -3-ω-iodoalkyl derivatives to provide tricyclic systems using dicumyl peroxide as the sole reagent is studied. The method then is employed for the syntheses of 5-, 6-, and 7-membered fused quinazolinone analogues, including the natural products deoxyvasicinone and mackinazolinone. A xanthate-based oxidative radical cascade addition/cyclization process that allows the production of new menthol- and testosterone-quinazolinone conjugates, as well as the first total synthesis of leucomidine C, are also reported.
On the Synthesis and Reactivity of 2,3-Dihydropyrrolo[1,2- a ]quinazolin-5(1 H)-ones
Sutherell, Charlotte L.,Ley, Steven V.
, p. 135 - 144 (2016/12/24)
An improved, scalable synthetic route to the quinazolinone natural product 2,3-dihydropyrrolo[1,2-a]quinazolin-5(1H)-one is reported. The applicability of this method to analogue synthesis and the synthesis of related natural products is explored. Finally, reactivity of the scaffold to a variety of electrophilic reagents, generating products stereoselectively, is reported.
A compound for inhibiting acetylcholinesterase activity, and preparation method and uses thereof
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Paragraph 0049; 0050; 0051; 0052; 0053; 0054, (2016/10/08)
The invention discloses a compound for inhibiting acetylcholinesterase activity. The compound is characterized as the structure of the compound is described in the description, wherein n=1-3, R1 is selected from oxyl, halogen, alkyl, -H, -CN or -NO. Th
Reversible P(III)/P(V) redox: Catalytic aza-Wittig reaction for the synthesis of 4(3H)-quinazolinones and the natural product vasicinone
Wang, Long,Wang, Ying,Chen, Min,Ding, Ming-Wu
, p. 1098 - 1104 (2014/04/03)
The catalytic aza-Wittig reaction based on a phosphine/phosphine oxide catalytic cycle is reported. The by-product triphenylphosphine oxide (Ph 3PO) was reduced in situ to triphenylphosphine (Ph3P) with good chemselectivity so that the aza-Wittig reaction can be accomplished by using merely a catalytic amount of triphenylphosphine. The reaction has been demonstrated in an efficient synthesis of 4(3H)-quinazolinones and the natural product (S)-vasicinone in high yields, by using a catalytic amount of triphenylphosphine (5%) and the tetramethyldisiloxane/titanium tetraisopropoxide [TMDS/Ti(O-i-Pr)4] reductant system (81-95% yields and >99% ee).
Selective copper(II) acetate and potassium iodide catalyzed oxidation of aminals to dihydroquinazoline and quinazolinone alkaloids
Richers, Matthew T.,Zhao, Chenfei,Seidel, Daniel
, p. 1194 - 1201 (2013/07/26)
Copper(II) acetate/acetic acid/O2 and potassium iodide/tert-butylhydroperoxide systems are shown to affect the selective oxidation of ring-fused aminals to dihydroquinazolines and quinazolinones, respectively. These methods enable the facile preparation of a number of quinazoline alkaloid natural products and their analogues.
Antitussive effects of azepino[2,1-b]quinazolones
Nepali, Kunal,Bande, Mukunda S.,Sapra, Sameer,Garg, Atul,Kumar, Sunil,Sharma, Punita,Goyal, Rohit,Satti, Naresh Kumar,Suri, Om Parkash,Dhar, Kanaya Lal
experimental part, p. 1271 - 1277 (2012/08/28)
A series of azepino[2,1-b]quinazolones (C-1-C-16) have been synthesized and evaluated for their antitussive activity using citric acid-induced cough model in Guinea pigs. The compounds C-1-C-16 caused notable decrease in cough frequency and increase in co
Chemoselective aromatic azido reduction with concomitant aliphatic azide employing Al/Gd Triflates/Nal and ESI-MS mechanistic studies
Kamal, Ahmed,Markandeya, Nagula,Shankaraiah, Nagula,Ratna Reddy,Prabhakar,Sanjeeva Reddy,Eberlin, Marcos N.,Santos, Leonardo Silva
experimental part, p. 7215 - 7224 (2010/03/05)
Aluminium and gadolinium inflates catalyze the chemoselective reduction of aromatic azides to the corresponding amines in combination with sodium iodide. This mild chemoselective method has been applied to the synthesis of various aryl amines, C2azido-substituted pyrrolo[2,1-c]-[1,4]benzodiazepines, and fused[2,1b]quinazolinones by an intramolecular azido reduction tandem cyclization reaction. Interestingly, this methodology selectively reduces aryl azides with enhanced yields and proceeds in shorter reaction times than previous strategies. The mechanistic aspects have been investigated and the intermediates associated with this selective transformation have been intercepted and characterized by online monitoring of the reaction by ESI-MS.
One-pot synthesis of simple alkaloids: 2,3-Polymethylene-4(3H)- quinazolinones, luotonin A, tryptanthrin, and rutaecarpine
Jahng, Katherine Chae,Kim, Seung Ill,Kim, Dong Hyeon,Seo, Chang Seob,Son, Jong-Keun,Lee, Seung Ho,Lee, Eung Seok,Jahng, Yurngdong
experimental part, p. 607 - 609 (2009/04/06)
One-pot synthesis of various 2,3-polymethylene-4(3H)-quinazolinones from anthranilic acid, corresponding lactam and SOCl2 is described, which can be applicable to the synthesis of simple 4(3H)-quinazolinone-derived alkaloids, such as luotonin A, tryptanthrin, and rutaecarpine.
A polymer-assisted solution-phase strategy for the synthesis of fused [2,1-b]quinazolinones and the preparation of optically active vasicinone
Kamal, Ahmed,Devaiah,Shankaraiah,Laxma Reddy
, p. 2609 - 2612 (2008/09/16)
An efficient preparation of fused [2,1-b]quinazolinones has been developed utilizing polymer-supported reagents. (±)- Vasicinone was converted into its dione by oxidation with poly (4-vinylpyridiniumdichromate). An efficient method has been developed for the synthesis of (d)- and (l)-vasicinone via asymmetric reduction of pyrrolo[2,1-b]quinazoline-3,9-dione by employing NaBH4/Me3SiCl as the reducing agent and polymer-supported chiral sulfonamide as catalyst. Georg Thieme Verlag Stuttgart.
